PL94958B1 - - Google Patents
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- PL94958B1 PL94958B1 PL1974171858A PL17185874A PL94958B1 PL 94958 B1 PL94958 B1 PL 94958B1 PL 1974171858 A PL1974171858 A PL 1974171858A PL 17185874 A PL17185874 A PL 17185874A PL 94958 B1 PL94958 B1 PL 94958B1
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- 150000001875 compounds Chemical class 0.000 claims description 71
- -1 benzyl 2-phenyl ethyl Chemical group 0.000 claims description 60
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 22
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 11
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims description 4
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000002824 aphicidal effect Effects 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 239000003701 inert diluent Substances 0.000 claims description 3
- YJBMUOINMUUAQI-UHFFFAOYSA-N [[1-(dimethylamino)-3-(dimethylhydrazinylidene)-1-oxobutan-2-ylidene]amino] N,N-dimethylcarbamate Chemical group CN(C)N=C(C)C(C(=O)N(C)C)=NOC(=O)N(C)C YJBMUOINMUUAQI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
- 102100025854 Acyl-coenzyme A thioesterase 1 Human genes 0.000 claims 2
- 101710175445 Acyl-coenzyme A thioesterase 1 Proteins 0.000 claims 2
- 108010093488 His-His-His-His-His-His Proteins 0.000 claims 2
- 238000002329 infrared spectrum Methods 0.000 claims 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims 1
- 101100005001 Caenorhabditis elegans cah-5 gene Proteins 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241000689227 Cora <basidiomycete fungus> Species 0.000 claims 1
- 101100327795 Penaeus monodon CHH3 gene Proteins 0.000 claims 1
- NOABJNYOHPTKLL-UHFFFAOYSA-N [[1-(dimethylamino)-3-methoxyimino-1-oxobutan-2-ylidene]amino] N,N-dimethylcarbamate Chemical group CON=C(C)C(C(=O)N(C)C)=NOC(=O)N(C)C NOABJNYOHPTKLL-UHFFFAOYSA-N 0.000 claims 1
- JKAJNYKIFBUYKF-UHFFFAOYSA-N [[1-(dimethylamino)-3-methoxyimino-1-oxobutan-2-ylidene]amino] n-methylcarbamate Chemical group CNC(=O)ON=C(C(=O)N(C)C)C(C)=NOC JKAJNYKIFBUYKF-UHFFFAOYSA-N 0.000 claims 1
- 150000004652 butanoic acids Chemical class 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 241001124076 Aphididae Species 0.000 description 47
- 239000000203 mixture Substances 0.000 description 30
- 238000012360 testing method Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000002689 soil Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 13
- 238000005507 spraying Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 241000208241 Tropaeolum Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 235000016068 Berberis vulgaris Nutrition 0.000 description 7
- 241000335053 Beta vulgaris Species 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 235000004424 Tropaeolum majus Nutrition 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 241001095118 Aphis pomi Species 0.000 description 5
- 241000255749 Coccinellidae Species 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 241000207199 Citrus Species 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 241000721621 Myzus persicae Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 235000020971 citrus fruits Nutrition 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 235000021537 Beetroot Nutrition 0.000 description 3
- XFLOBLIVLYVEST-UHFFFAOYSA-N CC(=N)C(=NO)C(N)=O Chemical class CC(=N)C(=NO)C(N)=O XFLOBLIVLYVEST-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 241000220225 Malus Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000013068 control sample Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002420 orchard Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- KZPDOYCDYDTFPS-UHFFFAOYSA-N 2-hydroxyimino-3-iminopentanamide Chemical class CCC(=N)C(=NO)C(N)=O KZPDOYCDYDTFPS-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- FHSUFDYFOHSYHI-UHFFFAOYSA-N 3-oxopentanoic acid Chemical class CCC(=O)CC(O)=O FHSUFDYFOHSYHI-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 241000282485 Vulpes vulpes Species 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 230000021235 carbamoylation Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- PBZUAIHRZUBBAJ-HNQUOIGGSA-N (2e)-2-hydroxyiminoacetic acid Chemical class O\N=C\C(O)=O PBZUAIHRZUBBAJ-HNQUOIGGSA-N 0.000 description 1
- VCZQYTJRWNRPHF-UHFFFAOYSA-N 1,2-dioxin Chemical class O1OC=CC=C1 VCZQYTJRWNRPHF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- YHZBJNXFYPODJB-UHFFFAOYSA-N 2-hydroxyimino-3-methoxyimino-N,N-dimethylbutanamide Chemical compound CON=C(C)C(=NO)C(=O)N(C)C YHZBJNXFYPODJB-UHFFFAOYSA-N 0.000 description 1
- YYOAJGVOBRTMJJ-UHFFFAOYSA-N 2-hydroxyimino-3-methoxyimino-N-methylpentanamide Chemical compound CON=C(CC)C(=NO)C(=O)NC YYOAJGVOBRTMJJ-UHFFFAOYSA-N 0.000 description 1
- NXZLTPQEYLXQCH-UHFFFAOYSA-N 2-hydroxyiminoacetamide Chemical class NC(=O)C=NO NXZLTPQEYLXQCH-UHFFFAOYSA-N 0.000 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- SMEVIORASKVRNF-UHFFFAOYSA-N 4-hydroxyimino-3-oxobutanoic acid Chemical compound ON=CC(=O)CC(O)=O SMEVIORASKVRNF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241000273311 Aphis spiraecola Species 0.000 description 1
- 101000894524 Bos taurus Transforming growth factor-beta-induced protein ig-h3 Proteins 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 1
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 1
- 241000982105 Brevicoryne brassicae Species 0.000 description 1
- WNMWFGATINEGEJ-UHFFFAOYSA-N C(CCC)(=O)NNOC(N(C)C)=O Chemical compound C(CCC)(=O)NNOC(N(C)C)=O WNMWFGATINEGEJ-UHFFFAOYSA-N 0.000 description 1
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 101000638722 Homo sapiens Thimet oligopeptidase Proteins 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000005950 Oxamyl Substances 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000590524 Protaphis middletonii Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 241000722027 Schizaphis graminum Species 0.000 description 1
- 241000180211 Sitobion miscanthi Species 0.000 description 1
- 102100031293 Thimet oligopeptidase Human genes 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 210000002534 adenoid Anatomy 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- QCFLHGRJPSRFJT-UHFFFAOYSA-N ethyl 2-hydroxyimino-3-methoxyiminopentanoate Chemical compound CCOC(=O)C(=NO)C(CC)=NOC QCFLHGRJPSRFJT-UHFFFAOYSA-N 0.000 description 1
- IKOYRGVURWBMRT-UHFFFAOYSA-N ethyl n-phenylethanehydrazonate Chemical compound CCOC(C)=NNC1=CC=CC=C1 IKOYRGVURWBMRT-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 1
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- MVGBKLTYYAYYGY-UHFFFAOYSA-N pyruvic oxime Chemical compound ON=C(C)C(O)=O MVGBKLTYYAYYGY-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36960673A | 1973-06-13 | 1973-06-13 | |
| US05/463,987 US4059623A (en) | 1973-06-13 | 1974-04-25 | Butyramides and butyrates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL94958B1 true PL94958B1 (de) | 1977-09-30 |
Family
ID=27004643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1974171858A PL94958B1 (de) | 1973-06-13 | 1974-06-12 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4059623A (de) |
| JP (1) | JPS5757445B2 (de) |
| AR (1) | AR216040A1 (de) |
| BR (1) | BR7404848D0 (de) |
| CA (1) | CA1031341A (de) |
| CH (1) | CH600763A5 (de) |
| CS (1) | CS197232B2 (de) |
| DD (1) | DD118511A5 (de) |
| DE (1) | DE2428070C2 (de) |
| DK (1) | DK314374A (de) |
| ES (1) | ES427185A1 (de) |
| FR (1) | FR2233317B1 (de) |
| GB (1) | GB1438426A (de) |
| IE (1) | IE39284B1 (de) |
| IL (1) | IL45017A (de) |
| IT (1) | IT1049223B (de) |
| NL (1) | NL7407926A (de) |
| NO (1) | NO139220C (de) |
| PH (1) | PH11491A (de) |
| PL (1) | PL94958B1 (de) |
| SE (1) | SE7406469L (de) |
| YU (2) | YU166674A (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4657904A (en) * | 1978-11-03 | 1987-04-14 | Union Carbide Corporation | Sulfur-containing bis-imino carbamate compounds, pesticidal composition and use |
| US4435421A (en) | 1978-11-03 | 1984-03-06 | Union Carbide Corporation | Biocidal sulfur-containing bis-imino carbamate compounds |
| US4725682A (en) * | 1978-11-03 | 1988-02-16 | Rhone-Poulenc Nederland, B.V. | Biocidal sulfur-containing bis-imino carbamate compounds |
| DK0387499T3 (da) * | 1989-02-16 | 1994-02-14 | Bayer Ag | Substituerede oximethere samt deres anvendelse som pesticider |
| WO1998016499A1 (fr) * | 1996-10-15 | 1998-04-23 | Shionogi & Co., Ltd. | Derives d'oxime, derives d'hydrazone, et leur utilisation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2542812A (en) * | 1946-04-03 | 1951-02-20 | Walter H Hartung | Preparation of aminoacidamides |
| US3849481A (en) * | 1970-12-11 | 1974-11-19 | Allied Chem | Hydrogenation of lysine precursors |
-
1974
- 1974-04-25 US US05/463,987 patent/US4059623A/en not_active Expired - Lifetime
- 1974-05-15 SE SE7406469A patent/SE7406469L/xx unknown
- 1974-05-22 IE IE1098/74A patent/IE39284B1/xx unknown
- 1974-06-07 CS CS744058A patent/CS197232B2/cs unknown
- 1974-06-11 ES ES427185A patent/ES427185A1/es not_active Expired
- 1974-06-11 CA CA202,336A patent/CA1031341A/en not_active Expired
- 1974-06-11 JP JP49065669A patent/JPS5757445B2/ja not_active Expired
- 1974-06-11 DE DE2428070A patent/DE2428070C2/de not_active Expired
- 1974-06-11 IT IT23856/74A patent/IT1049223B/it active
- 1974-06-12 BR BR4848/74A patent/BR7404848D0/pt unknown
- 1974-06-12 CH CH805974A patent/CH600763A5/xx not_active IP Right Cessation
- 1974-06-12 PL PL1974171858A patent/PL94958B1/pl unknown
- 1974-06-12 FR FR7420317A patent/FR2233317B1/fr not_active Expired
- 1974-06-12 AR AR254171A patent/AR216040A1/es active
- 1974-06-12 GB GB2608774A patent/GB1438426A/en not_active Expired
- 1974-06-12 DK DK314374A patent/DK314374A/da unknown
- 1974-06-12 IL IL45017A patent/IL45017A/xx unknown
- 1974-06-12 DD DD179108A patent/DD118511A5/xx unknown
- 1974-06-12 NO NO742129A patent/NO139220C/no unknown
- 1974-06-13 PH PH15934A patent/PH11491A/en unknown
- 1974-06-13 YU YU01666/74A patent/YU166674A/xx unknown
- 1974-06-13 NL NL7407926A patent/NL7407926A/xx not_active Application Discontinuation
-
1981
- 1981-09-09 YU YU02156/81A patent/YU215681A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL45017A (en) | 1978-01-31 |
| NL7407926A (de) | 1974-12-17 |
| JPS5035336A (de) | 1975-04-04 |
| DE2428070C2 (de) | 1985-10-10 |
| IT1049223B (it) | 1981-01-20 |
| IL45017A0 (en) | 1974-09-10 |
| SE7406469L (de) | 1974-12-16 |
| BR7404848D0 (pt) | 1975-09-23 |
| CH600763A5 (de) | 1978-06-30 |
| NO742129L (de) | 1975-01-06 |
| IE39284L (en) | 1974-12-13 |
| DK314374A (de) | 1975-02-03 |
| YU166674A (en) | 1982-02-28 |
| NO139220B (no) | 1978-10-16 |
| FR2233317B1 (de) | 1978-01-13 |
| JPS5757445B2 (de) | 1982-12-04 |
| ES427185A1 (es) | 1976-09-16 |
| AR216040A1 (es) | 1979-11-30 |
| DD118511A5 (de) | 1976-03-12 |
| FR2233317A1 (de) | 1975-01-10 |
| YU215681A (en) | 1982-08-31 |
| CA1031341A (en) | 1978-05-16 |
| US4059623A (en) | 1977-11-22 |
| AU6999674A (en) | 1975-12-11 |
| IE39284B1 (en) | 1978-09-13 |
| NO139220C (no) | 1979-01-24 |
| GB1438426A (en) | 1976-06-09 |
| PH11491A (en) | 1978-02-01 |
| DE2428070A1 (de) | 1975-01-09 |
| CS197232B2 (en) | 1980-04-30 |
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